N-Ethyltryptamine

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N-Ethyltryptamine
N-Ethyltryptamine.png
NET 3D.png
Clinical data
Other namesNET; NETP; Ethyltryptamine
ATC code
  • None
Legal status
Legal status
Identifiers
  • N-ethyl-2-(1H-indol-3-yl)ethan-1-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C12H16N2
Molar mass 188.274 g·mol−1
3D model (JSmol)
Melting point 87 to 88 °C (189 to 190 °F)
  • CCNCCc1c[nH]c2ccccc12
  • InChI=1S/C12H16N2/c1-2-13-8-7-10-9-14-12-6-4-3-5-11(10)12/h3-6,9,13-14H,2,7-8H2,1H3 Yes check.svgY
  • Key:TZWUSTVNAVKAPA-UHFFFAOYSA-N Yes check.svgY
   (verify)

N-Ethyltryptamine (NET), also abbreviated as NETP, is a tryptamine that is structurally related to N-methyltryptamine (NMT) and the psychedelic drugs N,N-dimethyltryptamine (DMT) and N,N-diethyltryptamine (DET). [1]

Contents

Use and effects

Alexander Shulgin included NET as an entry in his book TiHKAL (Tryptamines I Have Known and Loved). [1] However, he stated that it had been subjected only to modest human trials and that no active dose level had been identified. [1]

Pharmacology

Pharmacodynamics

NMT activities
TargetAffinity (Ki, nM)
5-HT1A IA
5-HT2A 38 (EC50 Tooltip half-maximal effective concentration)
99% (Emax Tooltip maximal efficacy)
SERT 19a (EC50)
NET Tooltip Norepinephrine transporter3,862a (EC50)
DAT Tooltip Dopamine transporter6,660a (EC50)
Notes: The smaller the value, the more avidly the drug interacts with the site. Footnotes:a = Neurotransmitter release. Sources: [2]

NET has been found to act as a potent serotonin 5-HT2A receptor full agonist and a selective serotonin releasing agent. [2] It is inactive at the 5-HT1A receptor. [2]

Chemistry

Synthesis

The chemical synthesis of NET has been described. [1]

Analogues

Analogues of NET include N-methyltryptamine (NMT), dimethyltryptamine (DMT), methylethyltryptamine (MET), and diethyltryptamine (DET), among others. [1]

See also

References

  1. 1 2 3 4 5 NET Entry in TIHKAL
  2. 1 2 3 Blough BE, Landavazo A, Decker AM, Partilla JS, Baumann MH, Rothman RB (October 2014). "Interaction of psychoactive tryptamines with biogenic amine transporters and serotonin receptor subtypes". Psychopharmacology (Berl). 231 (21): 4135–4144. doi:10.1007/s00213-014-3557-7. PMC   4194234 . PMID   24800892.
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